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Jack Ryan, a surfer and small-time thief, has a fight with the intimidating Lou Harris, involving a baseball bat. Harris is a foreman on a Hawaii construction site run by duplicitous millionaire Ray Ritchie. When Jack is released from jail, both the police and Ritchie's business partner, Bob Rogers, Jr., tell Jack to leave the island. However, Judge Walter Crewes takes a liking to Jack and offers him a place to stay and a job as a handyman at a small resort of beach-front bungalows that the Judge owns. Jack has treacherous encounters with Harris and Rogers, Jr., on numerous occasions.

Ritchie has all his (substantial) property registered in the name of his wife, Alison. He is also cheating on his wife with a much younger mistress, Nancy Hayes. When Nancy takes an interest in Jack, the Judge warns him that she likes "the criminal type" and cannot be trusted. Jack is falling for Nancy, and the two break into houses for fun and profit.

Nancy suggests to Jack a scheme to steal $200,000 ($259,000 today) that Ritchie keeps for bribes and mob business. She arranges for Jack to sneak into Ritchie's house to steal the money from his safe. Jack arrives to find that Nancy has poisoned Ritchie, in a conspiracy with Alison. Nancy has set up Jack to be Ritchie's "killer", with Alison to shoot him dead as an intruder. It turns out that the Judge is Alison's lover and has been part of the conspiracy, with the two promising to give Nancy the $200,000 for her part. Jack manages to steal the money from the safe and narrowly escapes, leaving Alison and the Judge to set up Nancy as Ritchie's killer.

Alison and the Judge are seen sailing on Ritchie's yacht, disposing of his body in the ocean. Nancy is seen in disguise, trying to escape the island before she's arrested for Ritchie's murder. Jack drives past Nancy in a limousine, stopping to wish her well and refusing to help her after she set him up. He gets back in the limo, with the money and a beautiful vacationer named Number 9 he met while working at the Judge's resort.

George Armitage was given a copy of Sebastian Gutirrez's script by Steve Bing.

The Big Bounce, the book, when you break it down, is basically an act and a half. It’s not a real three acts. So you’re going to have to add half of the picture. So right away you’re in trouble with somebody like Elmore, who I considered to be an absolutely brilliant writer. So he worked on the script with me, he gave me notes, and the notes are classic, they’re great.[1]

On the first day of pre production, Armitage was hit in the eye with a piece of lava rock and contracted a virus. The director came down with an infection with two weeks left to shoot and had to go to the hospital. Production shut down but Armitage says "Fortunately it was right at Christmas, so it turned into a Christmas break that we hadn’t planned on, and I completed the picture afterwards."[1]

Armitage says that despite this the film was very pleasant. "Now, being in Hawaii was probably a great deal of that. But it was just an extraordinary experience, and I credit the producer, Steve Bing, with that. He put up his own money, and I think he had $250,000 in bar bills, just picking up drinks for the crew and cast for all that time. So he couldn’t have been more wonderful."[1]

Armitage says the film encountered troubles in post production when Steve Bing suffered a crisis of conscience:

He was getting advice from people who’re in the money business, and he felt that to have a chance to get his money back, he should go PG-13. It was very difficult for some people to understand that when you take away the reality of these people, the way they speak, what they do—these are important elements of the movie that make it work. Whether they would’ve made it a financial success I don’t know, but they make the movie work, and if the movie works, you have more of a chance of more people seeing it.... The first time we showed the film, it came in at an NC-17 instead of an R. And it was unreleasable in that form. So I said: “We’ll make it an R.” Grosse Pointe Blank was an R, we made it for $7 million and it probably made $45 million lifetime, all in. But they said: “You can’t make an R-rated comedy, they don’t make money.” That’s what they were saying in 2004. Since then, of course, a lot of R-rated comedies have done beautifully. So I said: “Look, I’m not going to oversee the destruction of my own movie, there’s no way. If you go to a PG-13, you’re going to eliminate Elmore Leonard from this movie.” The language, there’s some incredible love scenes… But the decision was made—they felt that they had to do that, so I said: “Goodbye.” I left the picture after my second cut. We’d already had two very, very good previews: in the 80s, up to the 90s. I don’t think I’ve even looked at the release print. A lot of the cuts were language and nudity. Owen and Sarah were good sports, very generous with themselves. But when people ask to see my last movie, I show them my cut of The Big Bounce, I don’t show them what’s out there. It isn’t absolutely complete, but I think it could have been a far, far better film.[1]

The film has received generally negative reviews; review aggregate Rotten Tomatoes reports that 16% of critics have given the film a positive review based on 134 reviews, with an average score of 4.1/10;the consensus states: "Lazily crafted and light on substance, The Big Bounce takes few chances and strands its promising cast in a subpar adaptation that fails to do its source material justice".[4]